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Patented Mar. 30, 1926.

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2532. n. wears, or Perms enov's, -nsw senses, asszen'on' re n. it. in: iEfiHi 10a NEMGUBB COMBANY, GE-WILMINGTQN, DELAWARE, CGRNRQTIQN. Q3

wens. I rnoorzss or mxme mrnamsonns. v v i a No Brewing. Application area September 11,1920. serial No. 410,979.. To (iZZ whom it 1mg concern 4 lhe excess alcohol is distilled off and thei Be it known that I, EA L, HQ -Wnrrrz, a nitranisole is drawn oil. after washing with citizen of the United States, and a resident hot water to remove the sodium chloride of 'PennwGrove, in the countyoi? Salem and nitro-phenolates which are also formed I and State of New Jersey, have invented a in thereaction.

certain new and useful Process ,of Making; The reaction is preferably carried out, in N itranisoles, of which the following is a enameled or glasslined apparatus; iron may specification. beused but in the case the product is :usu-

My invention relatesjo' the production 01. ally larger than that prepared in the other 5.

nitranisoles, and consists essentially in conapparatus andwould probably haveto be -densing a nitrophenyl halide, such as nit-ropurified." chlorobenzene, with;methyl-alcohol, prefer- As examples of other ,nitranisoles which ably dilute, under pressure in the, presence may be produced according to my process ofan alkali such as sodium hydroxide. there may be; mentioned paraoiitranisole 6 In the preparation of nitranisoles from frompara-11itrochloroben'zene,and dinitsani nitrochlorobenzene, methyl alcohol, end a sole from dinitrochlorobenzene. caustic alkali, the main reaction is acco m- Although the temperature is preferably panied, under. certain conditions, by side maintained between 100 and 120. (3., either reactions such as reduction, which result in a higher or lower temperature may be used .65

29 the formation of What-are probably azo or without-departing from my invention.

azoxy compounds These not only diminish I claim I the yield of the desired product, but also 1. A process of makmgenitranisojle which make necessary a separation of the desired comprises heating under pressure and at a product fromthe impurities. -temperature'of from about l05'tol10" C. a 0

I have discovered that the aforesaid side nitrochlorobenzeneand methyl alcohol injthe reactions, and especially reduction, may be presence of Water and an alkali-metalhylargely avoided by carrying out the condendroxide. sation under pressure, and by using dilute 2. A process of making ortho-nitranisolc alcohol solution containing, say, from about at a temperature between. 100 and 120 0., 10 to of Water. Not only, is the yield ortho-nitrochlorobenzene an aqueous ofnitranisoles increased by proceeding in methyl alcohol solution containing from this manner, but a very great saving in time about 10 to 25% ofwaterin the presence of is effected, ascompared withv known pio'csodium hydroxide. essesi v 5 v 3. The process otmaking ortho-nitranisoie The invention may be illustrated by the which comprises heating under pressure,

following example of the preparation of and at a temperature between 100 and 120 ortho-hitranisole. C., one partof ortho nitrochlorobenzene, 0.28 to 0.30 parts caustic soda are dis three to six parts of methyl alcohol solution solved in 3-6 parts of -90% methyl alcocontaining from 10 to 20% of water, and hol- (1020% water) and after the addition about three-tenths of a part of sodium hyof one part of ortho nitro-chlorobenzene', the 'droxide.

autoclave is made air tight; The tempera- In testimony whereof I z tlix my signature. ture'is then raised to -110" C. and held for 442 hours, or until the reaction is EARL IL WEL'lZ;

finished.

methyl alcohol, that is, an 'aqueous methyl which comprises heatingunder pressur and v1926, upon theapplication of Earl H. VVeltz, of Penns Grove --im p rovement in Certificate of Correction. It/i8 hereby certified that in Letters Patent No. 1,578,943

New Jersey, for an Processes of Making Nlt-ramsoles, an error appears in the specification requiring correction as follows: Page 1 line 55, for the word larger? read darker; and that the said Letters Patent should be read with this correction therein that the same may conform to the Patent Oflice.

Signed and sealed'this 27th day of AprilfA. D. 1926.

record of the case in the M. J. MOOB- Acting Uommz'esz'o'ner of Patents.

, granted March 30, i 

